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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 85234Generated: October 30, 2026

Water → HCID 59410204, compound

https://huagongshe.com/reaction/85234

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactant1-Bromo-2-ChloroethaneHCID 7849—
ReactantCesium carbonateHCID 10796—
Reactant5-Chloro-N-({(5S)-3-[4-(3-hydroxy-2-oxopyridin-1(2H)-yl)-3,5-dimethylphenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamideHCID 59410174—
SolventN-methyl-2-pyrrolidoneHCID 13387—
ProductHCID 59410204HCID 59410204—

Reaction Conditions

Temperature60 °C

Reaction Steps

900 mg (1.89 mmol) of the compound from Example 72A and 1.36 g (9.49 mmol) of 1-bromo-2-chloroethane are dissolved in 30 ml of 1-methyl-2-pyrrolidone. 1.55 g (4.75 mmol) of caesium carbonate are added to the solution, and the mixture is stirred at 60° C. for 15 hours. Water is then added, and, after phase separation, the aqueous phase is extracted three times with tert-butyl methyl ether and three times with dichloromethane. The combined organic phases are washed successively with 1N aqueous sodium hydroxide solution and saturated sodium chloride solution and then dried over sodium sulphate. The drying agent is filtered off and the solvent is removed completely on a rotary evaporator. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:5). This gives 464 mg (45% of theory, purity according to LC-MS 74%) of the desired product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08846934B2
Source datasetuspto-grants-2014_09
ORD IDord-0a8d2d20ede645d0a2b087d79cb89fd2
Source noteuspto-grants-2014_09